380 Whippoorwill Rd

This charming cottage has been completely gut renovated, offering the perfect blend of modern comfort and timeless character. Thoughtfully redesigned from top to bottom, this home is the ideal retreat—whether you're looking for a weekend getaway or a full-time residence. Located just minutes from the heart of downtown Chappaqua and mere seconds from Chappaqua Crossing and Horace Greeley High School, and Whippoorwill Park, the location couldn't be more convenient.
Inside, you'll find a bright, open layout with high-end finishes throughout. Every detail has been carefully considered, new kitchen with custom cabinetry (2018) and sleek appliances to the spa-like bathrooms and cozy, sun-filled living spaces. The renovation preserved the home’s original charm while bringing in all the modern upgrades today’s buyers expect, including new systems, windows, and beautiful hardwood floors.
Outside, the property offers peaceful surroundings and just the right amount of space to relax or entertain, all while being close to everything Chappaqua has to offer—shopping, dining, schools, and easy train access to NYC. This move-in-ready cottage is a rare find in one of Westchester’s most desirable communities.